293751-04-9

Basic information

• Product Name: 1-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonoxymethyl-5-O-methanesulfonyl-β-D-ribofuranosyl)thymine
• Synonyms: 1-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonoxymethyl-5-O-methanesulfonyl-β-D-ribofuranosyl)thymine
• CAS NO: 293751-04-9
• Molecular Formula: C₂₂H₂₈N₂O₁₂S₂
• Molecular Weight: 576.59
• Mol File: 293751-04-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonoxymethyl-5-O-methanesulfonyl-β-D-ribofuranosyl)thymine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonoxymethyl-5-O-methanesulfonyl-β-D-ribofuranosyl)thymine(293751-04-9)
• EPA Substance Registry System: 1-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonoxymethyl-5-O-methanesulfonyl-β-D-ribofuranosyl)thymine(293751-04-9)

Safety Data

• Hazardous Substances Data: 293751-04-9(Hazardous Substances Data)

Upstream product

• 65-71-4 thymin 
• 293751-03-8 1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose 
• 63593-03-3 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose 
• 293751-01-6 3-O-benzyl-4-C-methanesulfonoxymethyl-5-methanesulfonyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose 
• 63593-02-2 3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose 
• 22331-21-1 1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose 
• 57099-04-4 3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 

Downstream Products

• 293751-05-0 (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonoxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 
• 293751-06-1 1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-erythro-pentofuranosyl)thymine 
• 219601-01-1 (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane 
• 293751-07-2 1-(3-O-benzyl-2,5-di-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl)thymine 
• 552856-48-1 (1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane 
• 552856-42-5 (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane 
• 625111-32-2 (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane 
• 552856-38-9 2,2'-anhydro-1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine 
• 552856-39-0 1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine 
• 552856-41-4 1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl]thymine 
• 552856-40-3 1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-2-O-trifluoromethanesulfonyl-β-D-threo-pentofuranosyl)-thymine 
• 552856-44-7 (1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane 
• 552856-43-6 (1R,3R,4R,7S)-1-benzoyloxymethyl-7-benzyloxy-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane 
• 1054637-17-0 (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-N-methyl-3-(4-amino-5-methyl-cytosine-1-yl)-2-oxa-5-azabicyclo[2:2:1]heptane 

Relevant articles and documents

NOVEL PROCESS FOR MAKING ALLOFURANOSE FROM GLUCOFURANOSE

The present invention relates to the manufacture of allofuranose from glucofuranose as defined in the description and in the claim. Allofuranos is an intermediate in the manufacture of oligonucleotides which can be used as a medicament.

Large scale synthesis of 2′-Amino-LNA thymine and 5-methylcytosine nucleosides

Thymine intermediate 17 has been synthesized on a multigram scale (50 g, 70 mmol) from starting sugar 1 in 15 steps in an overall yield of 73%, with only 5 purification steps. The key thymine intermediate 18 was obtained from 17 in a single step in 96% yi

A simplified and efficient route to 2′-O, 4′-C-methylene-linked bicyclic ribonucleosides (locked nucleic acid)

A novel efficient method for the synthesis of locked nucleic acid (LNA) monomers is described. The LNA 5′,3′-diols containing thymine, 4-N-acetyl- and 4-N-benzoylcytosine, 6-N-benzoyladenine, and 2-N-isobutyrylguanine as nucleobases were prepared via convergent syntheses. The method is based on the use of the common sugar intermediate 1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonoxymethyl- 5-O-methanesulfonyl-D-erythro-pentofuranose (8) that easily can be prepared from D-glucose in multigram scale. Four different nucleobases were stereoselectively coupled to 8 using a modified Vorbrueggen procedure to give the corresponding 4′-C-branched nucleoside derivatives. Subsequent ring closing furnished the protected LNA nucleosides. The 5′-O-mesyl groups were efficiently displaced by nucleophilic substitution using sodium benzoate. Saponification of the 5′-benzoates followed by catalytic removal of the 3′-O-benzyl groups afforded the free LNA diols. The exocyclic amino groups of adenosine and cytidine were selectively acylated to give 4-N-acetyl- or 4-N-benzoyl-LNA-C and 6-N-benzoyl-LNA-A. The isobutyryl group of guanine was retained during the preparation of 2-N-isobutyryl-LNA-G. The LNA-T diol and base-protected LNA diols can be directly converted into LNA-phosphoramidites for automated chemical synthesis of LNA containing oligonucleotides.